Top 10 Films Directed by Clint Eastwood

Next to Arnold Schwarzenegger, Clint Eastwood is probably the most famous living Hollywood legend still going around – and he hasn’t slept with anybody other than his wife. Eastwood is probably Arnie’s equal for the number of quotable lines uttered on-screen over his career: from the unforgettable “Go ahead, make my day” of Dirty Harry’s Sudden Impact, to the “Do you feel lucky, punk?” of Magnum Force, to Unforgiven’s “It’s a hell of a thing, killing a man” speech, Eastwood’s steely eyed glare and tough-guy persona appealed to the rough and ready common man of the 60’s and 70’s, when he made his name starring in a number of films from spaghetti westerns for Sergio Leonie, to hard-nut crime capers. Eschewing actual emotion for a flint-sharp sarcasm and straight-arrow ethic, Eastwood’s screen career burned brightly throughout the 60’s, appearing as The Man With No Name in the now eponymous Dollars Trilogy, as well as Coogan’s Bluff, Paint Your Wagon (a musical, no less) and Hang ‘Em High. This continued into the 70’s, with roles in the Dirty Harry franchise of films, Joe Kidd, High Plains Drifter, The Outlaw Josey Wales and Escape From Alcatraz among his most famous action/western works. His film roles in the 80’s and 90’s were a little more of a mixed bag, with major successes like Pale Rider in 1985 and Unforgiven in 1992 (as well as In The Line Of Fire the following year) standing alongside critical failures like White Hunter Black Heart and Firefox, although the majority of his output continued to be at least financially successful.

Along with being a major screen star, Eastwood turned his hand to directing with 1971’s Play Misty For Me, and since then has continued to direct as well as star in his own vehicles, the majority of the time. With a keen eye for character and a terrific sense of pacing, Eastwood’s directorial career hit its first high with Unforgiven, bringing in both the Best Director and Best Film Oscars (among others) at that year’s Academy Awards. Eastwood’s next major success would be during the mid 2000’s, when 2003’s Mystic River, and 2004’s Million Dollar Baby would go on to be nominated for the very same Oscars once more, Best Picture and Director (as well as Best Actor, Best Actress, Supporting Actor and Actress) – with Million Dollar Baby scooping the pool. As a director, Eastwood has never been afraid to tackle different genres, from the Westerns he loved, to crime dramas (Midnight In The Garden Of Good And Evil, Blood Work, Sudden Impact), romance (Bridges Of Madison County), the ethereal (Hereafter), action (The Rookie), adventure (Space Cowboys), biography (J Edgar), and even a duo of war films – Flags Of Our Fathers, and Letters From Iwo Jima. While his films haven’t always been met with astonishing levels of acclaim, there’s no denying that a perfect descriptor of an Eastwood production is “thoughtful insight” at the very least.

Over the course of his directorial career since Play Misty For Me, Eastwood’s made a further 31 films to-date, each one showing a more astute eye behind the camera, a developing story-telling ability, and delivering a more rounded, complete cinema experience. Here, we’ve distilled the 10 best Eastwood-helmed films to-date, and tried our very best to rank them in order of entertainment value, directorial prowess, and cinematic legacy.

Eastwood’s first foray behind the camera met with substantial positive acclaim at the time, and the film still holds up to this day. One of the early “stalker” films (which paved the way for films like Fatal Attraction and Disclosure) sees Eastwood playing a radio DJ who finds himself the recipient of some unwanted attention from a female fan. Eastwood’s deft handling of the mounting tension, as Jessica Walter’s Evelyn Draper becomes more and more obsessed and insane with Eastwood’s Dave Garver, showed the new director’s keen observational skill and nuanced storytelling ability in its embryonic form. While perhaps not quite as honed as the Eastwood of today, Play Misty For Me is a classic of its time, and remains a terrific entry into directing.

While I’m no bubbling romantic, there’s no denying the exquisite nature of this wonderful, wonderful film. A film I’d describe simply as “charming” in both execution and endeavor, Bridges features yet another great role for Meryl Streep, and a solid leading-man effort from Eastwood, as the National Geographic photographer out on assignment who falls for a farmers wife. A gentle study in love, Bridges is a must for the doe-eyed viewer among you.

Representing the gritty, seedy nature of 70’s cinema, Josey Wales is among my personal favorite Eastwood pleasures, not the least because it features a quite revealing performance from one Sondra Locke – Eastwoods soon-to-be partner. Pulpish and grimy, filled with a sense of gratuitousness of the era in which it was made, Josey Wales is almost the antithesis of later films like Unforgiven and Pale Rider – you almost feel like having a shower after watching it.

The second of Eastwood’s forays into World War II (following on from the US-based Flags Of Our Fathers), Letters tells the story of the landing of Iwo Jima from the Japanese perspective. In what can only be considered a brave, nay a bold move from Warners, who allowed an American director helm an essentially Japanese film, Letters turned out to be a revelation in War Cinema. Less bombastic than its contemporary cousins, like Saving Private Ryan and even Flags Of Our Fathers, Letters From Iwo Jima is more a character study than an action film, and a subtle, sublime one at that.

Of all Eastwood’s films, this is perhaps his most “fun”. Space Cowboys, uniting Eastwood with screen legends Tommy-Lee Jones, Donald Sutherland and James Garner for the first time, was sheer entertainment – the quartet of distinguished gentlemen play aging astronauts sent into space to salvage an aging satellite with on-board systems nobody’s worked with in forty years. With plenty of laugh-out-loud moments, as well as some touches of genuine drama and emotion, Space Cowboys is as close as Eastwood’s come to a cinematic “romp”.

Clint’s first Best Director gong came with this powerful character piece, about a former killer called back into action after a prolonged absence from the lifestyle to raise a family. Eastwood starred as Bill Mumy, alongside Morgan Freeman, as a pair of grizzled mercenaries, on the hunt for retribution against Gene Hackman’s cruel Little Bill Daggett – they seek the bounty set by a group of whores for the attack by Little Bill against one of their own. Powerful, filled with a realism we’d not seen in a Western to that point, Unforgiven is an extraordinary film event that has not dulled in the years since.

One of my personal favorite Eastwood films ever, next to High Plains Drifter, Pale Rider remains perhaps the great man’s most accomplished westerns, Unforgiven aside. Pale Rider has a simple premise: a mysterious stranger rides into a mining camp in the Old West and takes up the fight against an unscrupulous businessman to eradicate those miners from “his” land. Featuring one of Eastwood’s best quotes, “There’s nothing like a good piece of hickory”, as well as some terrific editing and a gangbuster finale, Pale Rider is among the most iconic western genre films of the modern era.

Clint’s second Oscar win comes out of this searing ensemble piece about death, abuse and honor. Sean Penn and Tim Robbins scooped Oscars for their acting work here, as brothers who are held captive by abusive pedophiles, before growing into men leading distinctly different lives. After the murder of one of their children, their past is once more brought into the spotlight as they seek to find the killers, which eventually leads to a shocking confrontation. Mystic River is a hard film to watch, due to the subject matter at hand, but it is a superb film in its own right, and easily slots into our top 3.

A powerhouse directorial effort from Eastwood, portraying a racist, bigoted and utterly unlikeable Veteran who sees his idyllic life in the suburbs slowly eroded by the increasing number of Vietnamese residents around him. Featuring a gob-smacking twist ending, perhaps the second most powerful Eastwood moment ever, Gran Torino is a subtle, amusing, searing story of overcoming prejudice and accepting that those who appear different from you actually aren’t.

Easily Eastwood’s best effort behind the camera, thanks mainly to a wonderful performance by Oscar winner Hilary Swank, and ably backed up by co-star (and fellow Oscar winner) Morgan Freeman and even Eastwood himself. Eastwood won the Oscar for best Director, and the film picked up the Best Picture gong, completing a two year triumph for Eastwood after the previous year nearly doing the same for Mystic River. Part sports film, part human drama, Million Dollar Baby is captivating, shocking, emotionally gut-punching, and most of all, superb entertainment.

Disagree with our choices? Think Blood Work should have been included somewhere in this list? Vent your spleen in the comments section below!!

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9 Thoughts to “Top 10 Films Directed by Clint Eastwood”

So many I haven't seen yet, but I just told a fellow blogger I'd watch Unforgiven soon. He certainly is a living legend, Rodney, but your comment here '…he hasn’t slept with anybody other than his wife' makes me laugh. Well not that we know of anyway, but I think he's been married several times right? In any case, great post!
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i never would've thought Space Cowboys was worth a watch, but your comments have convinced me to give it a shot. As for the rest of the list…i don't really do westerns, so i can't speak to that, but you got the rest of them right.
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" … there’s no denying that a perfect descriptor of an Eastwood production is 'thoughtful insight' at the very least."

Can't agree with that one … The Gauntlet was pretty bad; Firefox was as dull as dishwater and Sudden Impact and The Rookie were simply terrible (and childish to boot).

Interesting list, but Unforgiven would have been my number one and, much to your chagrin I'm sure, I would have pushed Pale Rider out and replaced it with Black Hunter, White Heart. Plus I think Bronco Billy is as good as Josey Wales. Also, and there are many who wouldn't agree, I thought A Perfect World was really good – IMO easily better than the psycho bitch film at number 10. Nevertheless, glad to see Iwo Jima gets a nod before Father Flags …

Two terms I'd use to describe Eastwood's work as a director are sentimental and old fashioned, which is kinda oxymoronic given we are talking about Dirty Harry and Blondie here ….

Some fair points here, Mark. Thanks for stopping by! I agree, Sudden Impact and The Rookie were pretty ordinary, although I remember Firefox a little differently…. maybe it was my youth at the time, but I remember really enjoying it. Maybe I'll have to give it another shot….

To be honest, I was tossing up whether to include Black Hunter White Heart somewhere in the list, but couldn't find room in the films I did include…. and you're right, there's no way I'd exclude Pale Rider at the expense of any of those left aside… 😉 A Perfect World was decent, sure, although I had a bit of a thing against Kevin Costner which sullied my appreciation of it.

I guess what we can draw from this is that as he progressed as a film-maker, through the years, is that he learned and honed his style and methodology, and you'd have to agree that the bulk of his more recent films are superior than those of his earlier CV…. Would you agree, Mark?

"…. and you'd have to agree that the bulk of his more recent films are superior than those of his earlier CV…."

Yes Rodney, I wholeheartedly agree.

Still, I'm surprised that someone who liked Dances With Wolves could let the presence of Costner sully his appreciation of A Perfect World.

Speaking of which, did you see the thing about silent cinema on SBS last week where they showed a bit of the train station shoot out in The Untouchables while comparing it with the Odessa steps sequence in Potemkin? Made me want to watch the De Palma film again (for the 50th time) …

Ha ha, my relationship with Coster is a bit hit-and-miss – I think it depends on the film he's in, actually. Dances With Wolves works well in spite of Costner's leading role; I don't think he's bad, just lacking in the emotional range the film needed (but hey, who am I to criticize – it won a bunch of Oscars). Films like Open Range and Wyatt Earp (a review of the latter of which is coming up here in a few weeks) work WITH Costner's performance ability rather than against it. It's not that I don't like Costner per se, I just think he's suited to a particular kind of role, and often he tries to move too far outside his range as an actor.

Yes, I did see that SBS doco on film (I think it was called "The History of Film" or something equally as grand), but I haven't watched it yet – it's on the DVR waiting for me to spend an hour investing in it. I think it was part 9 or something, so I'd be keen to see the rest of the episodes. Must look for it on DVD.